Style Tips From the Men Who Dress America

Tommy Hilfiger

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Hilfiger in front of a Jean-Michel Basquiat painting in his New York apartment. He wears clothing from the Tommy Hilfiger fall/winter 2013 collection.

Credit: Photograph by Joshua Jordan

Tommy Hilfiger founded his company in 1984 and saw it break big as the official clothier of hip-hop's nineties boom. Thirty years later, the upstate New York native has taken to mining the past for glitz, pillaging rakish U.K. finery for ideas, and cribbing from his latest muse: Jay Gatsby. The designer divides his time between New York and Miami, cities where he and his wife can chase down the contemporary art they collect: "I'm on a Miami kick right now. I hadn't been in a while, but we went to Art Basel and wound up buying a house."

Don't Call It a Man Purse"I treat my jacket like it's my briefcase. I'll have sunglasses, a handkerchief, a pen, a wallet, a cell all in there. We put ticket pockets on many of our suit jackets, because they can hold keys, any kind of change – and we put a cell phone pocket inside every jacket we make now, too."

Testing Patterns"I love English patterns. They're all over my fall line, mixed together in different scales – herringbone, houndstooth, glen plaid. I like to see them exaggerated and blown up or really miniaturized. They've been around for years, but I wanted to change them and make them fresh."

No Rules"You used to have to put away whites after Labor Day – now it's just about whatever looks good and is comfortable, year-round. For fall we made an off-white suit in 7.5-ounce tropical wool. You can wear the jacket with dark trousers or the white trousers with a navy blazer, or wear a black bow tie with the whole thing and go formal."